Henry is one of the most successful Massachusetts businessmen ever. He owns the Boston Red Sox and Liverpool F.C. Both of these teams experienced glory under his charge but he also made mistakes. Many Liverpool fans have mixed feelings about Henry because they don’t trust his intentions (via The Mirror).
One of his mistakes saw him attempt to trademark the name ‘Liverpool.’ In the end, a court ruled against this but it damaged his image in the U.K. He also supported the creation of a new European Super League. This brought immense criticism from fans who accused him of ripping the club’s history apart.